page_title: Penicillin
section_title: Biosynthesis
hierarchical_section_title: Penicillin / Production / Biosynthesis
caption_attribution_description: Penicillin biosynthesis
context_page_description: Penicillin is a group of antibiotics, derived originally from common moulds known as Penicillium moulds; which includes penicillin G, penicillin V, procaine penicillin, and benzathine penicillin. Penicillin antibiotics were among the first medications to be effective against many bacterial infections caused by staphylococci and streptococci. They are still widely used today, though many types of bacteria have developed resistance following extensive use.
  About 10% of people report that they are allergic to penicillin; however, up to 90% of this group may not actually be allergic. Serious allergies only occur in about 0.03%. Those who are allergic to penicillin are most often given cephalosporin C because of its functional groups. All penicillins are β-lactam antibiotics, which are some of the most powerful and successful achievements in modern science.
  Penicillin was discovered in 1928 by Scottish scientist Alexander Fleming. People began using it to treat infections in 1942. There are several enhanced penicillin families which are effective against additional bacteria; these include the antistaphylococcal penicillins, aminopenicillins and the antipseudomonal penicillins.
context_section_description: Overall, there are three main and important steps to the biosynthesis of penicillin G (benzylpenicillin).
  The first step is the condensation of three amino acids—L-α-aminoadipic acid, L-cysteine, L-valine into a tripeptide. Before condensing into the tripeptide, the amino acid L-valine must undergo epimerization to become D-valine. The condensed tripeptide is named δ-(L-α-aminoadipyl)-L-cysteine-D-valine (ACV). The condensation reaction and epimerization are both catalyzed by the enzyme δ-(L-α-aminoadipyl)-L-cysteine-D-valine synthetase (ACVS), a nonribosomal peptide synthetase or NRPS.
  The second step in the biosynthesis of penicillin G is the oxidative conversion of linear ACV into the bicyclic intermediate isopenicillin N by isopenicillin N synthase (IPNS), which is encoded by the gene pcbC. Isopenicillin N is a very weak intermediate, because it does not show strong antibiotic activity.
  The final step is a transamidation by isopenicillin N N-acyltransferase, in which the α-aminoadipyl side-chain of isopenicillin N is removed and exchanged for a phenylacetyl side-chain. This reaction is encoded by the gene penDE, which is unique in the process of obtaining penicillins.
caption: Penicillin G biosynthesis
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